12 Best Upselling Examples From SaaS [Examples and Best Practices]

Looking for upselling examples that you can apply in your SaaS to drive growth with account expansion?

It’s NOT as simple as: “Hey, you bought this product. Why not go for this higher tier plan for $5 extra?”

Upselling for SaaS requires engaging with your users at the right moment with the right in-app message.

In this article, we'll go over what upselling and cross-selling are in SaaS companies, how to measure their success, and what are some of the best examples of upselling tactics to kick-start the user upgrade process.

So, let’s get started!


  • Upselling SaaS means driving more revenue and increasing the customer lifetime value through subscription upgrades and add-ons.
  • Cross-selling involves adding complementary products or add-ons to the customer’s initial purchase.
  • If you are looking to increase the customer lifetime value by using upselling, you should look at automating in-app messages to communicate value at the right time.
  • Expansion MRR is the main KPI to track revenue growth you gain from current customers through upsells, add-ons, and cross-sells.

Good Upselling Examples we cover:

  • Slack uses well-timed in-app messaging to turn free users into paying customers.
  • Dropbox uses persistent upsell prompts to remind users of their free accounts' limitations.
  • Intercom doesn’t restrict the use of their series features but reminds the users that they have to upgrade to go live using well places tooltips.
  • Zapier does a great job in using contextual upgrade prompts triggered when the user reaches their account limits.
  • Asana offers free trials of premium features to its freemium users ( what a mouthful, right?)
  • Airtable increases premium users by pairing in-app messages upgrade prompts with email campaigns.
  • Spotify does a great job at strategically positioning upgrade prompts within its platform right when the users need them.
  • Harvest displays premium functionality alongside free features to show users the premium options.
  • Loom is great with timing, and they have more than one upselling prompt.
  • Figma’s Figjam tests placement and message types when free trials are about to expire
  • Want to use product experiments and split-test your in-app messaging? Get a Userpilot demo and see how you can use segmentation and trigger contextually upgrade messages.

What is upselling in SaaS?

Upselling SaaS means driving more revenue and increasing the customer lifetime value through subscription upgrades and add-ons. When your product has a freemium version or a trial, upgrading free users or free trial users to paid accounts is also considered an upsell.

Upselling vs cross-selling

The difference between upselling and cross-selling is in their names.

Upselling is the strategy of persuading customers to purchase a similar product with premium features or additional resources. On the other hand, cross-selling is the technique of selling complementary products to the initial purchase.

upselling examples vs cross-selling
Upselling vs cross-selling

Suppose you own a marketing automation platform with tiered pricing plans -Bronze, Silver & Gold – each with its unique features. If a customer wants to buy the Bronze plan and you offer them a Gold plan to get better support and features, that’s an upsell. If you offer them a CRM alongside their purchase, that’s a cross-sell.

In this article, we'll focus on upselling techniques rather than cross-selling and how you can do it contextually with in-app messages.

How do you upsell a SaaS product?

Upselling and cross-selling are all about communicating with users and explaining to them how they can benefit from upgrades and additional features. But to do this in person could be time-consuming and not efficient.

This is why if you are looking to increase the customer lifetime value by using upselling, you should look at automating in-app messages to communicate value at the right time.

But first, let's see how to measure success.

How do you measure upselling in SaaS companies?

Expansion MRR helps you track the monthly recurring revenue generated from existing customers who have upgraded their existing subscription plans.

You can calculate the Expansion MRR rate using this formula:

Expansion MRR rate = (Expansion MRR at the end of the month) – (Expansion MRR at the beginning of the month) divided by the Expansion MRR at the beginning of the month and multiplied by 100.

Best upselling examples (SaaS)

Now that we understand how to measure upselling, let's look at some of the most common upselling tactics used by SaaS brands to generate expansion monthly recurring revenue.

Slack uses FOMO to drive freemium to paid upgrades

It’s much easier to upsell customers when your message is relevant, timely, and not forced.

Slack uses well-timed in-app messaging to tempt free users to upgrade to a premium plan by showing them what they are missing out on.

Slack limits free users to 10,000 searchable messages. Once users reach the searchable limit, they get the first upsell message, which reminds them that they are missing out on some messages due to their free plan limits.

slack upselling examples

Dropbox and its continuous reminders

Most SaaS companies wait for their new users to exhaust all their current plans resources before sending them an upsell offer.

This is wrong! and Dropbox has proved us right.

Dropbox uses upsell prompts to remind users of their free accounts' limitations and offers them the opportunity to upgrade anytime to get additional space.

dropbox upselling examples


Intercom is a good example of a SaaS brand that shows its users value and gives them a strong reason to upgrade.

Intercom doesn’t restrict the use of its series features, but it reminds the user that they have to upgrade to go live. In other words, the users get to try premium features and experience the value, giving them a strong reason to want to upgrade.

intercom upselling examples

Intercom also uses small tooltips with upgrade messages to remind users about the premium features.

intercom upselling examples

SquareSpace prompt upgrades

You don't always have to hide a premium feature from your UI to nudge users to upgrade.

SquareSpace gives users a glimpse at what they can get but through a Blurred Screen, then use a banner that notifies users that they need an upgrade.

Let's say you signed up for SquareSpace's personal plan and got access to all the features that allowed you to publish your website but now you're getting some comments on your site and want to check analytics to know how many people visit.

You go on the analytics dashboard, and you see the image below. What would be your reaction?

Let me guess…

First, you'd be excited because you can see through the blurry screen that there are visitors on your site. Secondly, you'd be prompted to upgrade as soon as possible because you want to see more detail.

squarespace upselling examples
SquareSpace upgrade banner

Zapier contextual upgrade prompts to existing customers

Customers don't like to be forced or pushed to make an upgrade. The last thing you should do is shove your offer on their faces at every given opportunity – it can be annoying.

Instead, it's best to tie your prompts to your customers' actions to assist them in understanding what they want and what they can get from an upgrade.

For instance, Zapier triggers a modal window when a customer tries to add a new Zap but they've reached the limit of their plan. Adding the Upgrade Now button there, makes it easy for the user to take action too.

zapier upselling examples
Zapier upgrade prompt

Asana promotes paid features to power users offering them trials

Offering trials to premium features is a great upselling strategy. Once customers experience the value of the paid features first-hand, they will be more likely to upgrade at the end of the trial.

Asana is known for applying this strategy of showing off its premium features to certain users by showcasing the main benefits of the features with an in-app modal.

asana upselling examples
Asana offering free trials of premium features

Airtable combines in-app message upgrade prompts with emails

In-app messaging is a great method for communicating with your existing customer, but this only works if your customer is inside the app.

Pairing your upgrade prompt with an engaging email is a great way to succeed in upselling.

Airtable uses emails to connect with its users outside of the app. They have a newsletter that provides new customers with a breakdown of a few of Airtable’s premium options and offers suggestions to help the user get the most out of their product.

airtable upselling examples email
Airtable email


Let’s be real. Your customers will most likely not go to your pricing page to learn about your pricing plans.

Instead of waiting for them to search for it, make them rather conscious of your premium options by strategically positioning reminders within your platform.

Spotify, allows free customers to skip six tracks per hour, and then they are prompted to upgrade to a premium account. The premium features are built into the user experience, which allows the listener to see it in context and know how it will profit them.

spotify upselling examples

Harvest includes free and premium features

FOMO is a real thing. And how better way to trigger it than displaying premium features on your UI but making them unavailable for non-paying users.

Harvest, a time tracking software, displays premium functionality alongside free features to show users what they are missing out on.

harvest upselling examples
Harvest upsell tooltip

From the image above, you can see the “import” feature is grayed out. Hovering over it shows a pop-up box with an inline upgrade prompt hyperlink, making it easy for users to upgrade when they need more than the basic functionality of the app.

Loom uses upgrade prompts when you reach the account limits

Upselling is about understanding your customers, identifying upsell opportunities, and knowing the right time to ask for that upgrade. Loom does this perfectly.

Loom allows you to record videos on their free plan, but once you hit the 5-minute limit, an upsell prompt tells you how you can get unlimited recording time if you upgrade.

This upsell modal is perfect because it shows they understand their customer and are great with timing.

loom upsell modal
Loom upsell modal

Loom tells you about premium features at the right time

Loom is not just great with timing. It also uses more than one upselling prompt.

The message above was triggered by the free account limits, but what if the user constantly needs to record less than 3-minute videos? The above message would look out of context, right?

Loom went a step further to create another prompt to tease their users with a premium feature that has nothing to do with the video's length.

loom upsell modal
Loom upsell modal

Figma’s Figjam renewal reminders banners of different sizes

One of the best times to remind users to upgrade is when the free trial period is due to end. You might be thinking, “Won’t I lose them by asking them to upgrade to a paid version before their renewal date?”

No, you won’t. If you’ve provided value throughout the trial period – and have established yourself as a helpful resource/tool – a reminder is likely to work to your advantage.

Figma does this best by seamlessly blending upgrade messages inside the UI. They also use a mix of short and long messages and different placements to test which message is more effective.

figma upsell banners

Create upgrade prompts and target the right users with Userpilot

Are you looking to implement any of the upselling tactics described in this article?

You can do it all using segmentation capabilities to ensure your in-product messages show to the right user at the right time.

You can build modals, slideouts, tooltips, and banners and target customers contextually with your upgrade messages.

userpilot segmentation dashboard
Userpilot segmentation

Use product experiments and split-test your in-app messaging to optimize results and improve important SaaS metrics such as expansion MRR rate and others.

Userpilot makes it easy for your SaaS business to generate expansion revenue by creating upsell opportunities and prompting upgrades without writing a single line of code.


As we’ve established, upsells are 20x better than cross-sells. But you need the right strategy and techniques.

In this article, we’ve looked at some of the upselling strategies used by SaaS companies to generate more revenue and increase customer retention.

Want to build product experiences code-free? Book a demo call with our team and get started! Check out the banner below for more information.

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